Numerous medicinally important compounds are chiral. Compounds which are chiral by virtue of hydrogen-deuterium substitution have played an important role in the elucidation of biomedical mechanisms. However, general methods for the asymmetric chemical synthesis of molecules of these types have not yet been developed. We propose to investigate the chemistry of a new class of chiral organorhenium complexes. In preliminary experiments, we have observed that certain of these complexes can transfer their chirality from rhenium to ligating carbon in 100% optical yield. Since this chirality transfer may be electronic rather than steric in origin, a general method for asymmetric synthesis might be in hand. Among many objectives, we intend to: (a) demonstrate the utility of these in preparing a wide variety of organic molecules which are chiral by virtue of hydrogen-deuterium substitution, (b) investigate their utility for the preparation of organic molecules with chiral methyl groups (X-CHDT) and conventional secondary (X-CHRR') and tertiary (X-CRR'R") chiral centers, (c) attempt to use vinyl rhenium complexes for the expedient asymmetric synthesis of organic molecules with two adjacent chiral centers, (d) investigate the use of rhenium carbene complexes for asymmetric olefin cyclopropanation, (e) attempt the preparation of rhenium nu 1-diene and rhenium peracid complexes which may be useful for asymmetric Diels-Alder and epoxidation reactions. Improved syntheses of several types of medicinally important compounds are anticipated.